Bromoform → 5-bromo-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile

HRID 919170Notes

Reaction equation

HRID 919170 reaction equation
N[C:2]1[N:6]([C:7]2[C:12]([F:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([C:23]([F:26])([F:25])[F:24])=[O:22].N(OCCC(C)C)=O.C(Br)(Br)[Br:36]>>[Br:36][C:2]1[N:6]([C:7]2[C:12]([F:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([C:23]([F:26])([F:25])[F:24])=[O:22]

Participants

4

Reactant 3

HCID 5558BromoformHCID 8053Isoamyl Nitrite2×HCID 898587905-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile

Product 1

HCID 898588205-bromo-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrileYield 73%

Conditions

Temperature
60 °C

Procedure

To a solution of 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile (130 g, 310.3 mmol, 1.00 eq.) in CHBr3 (520 mL) was added dropwise isoamyl nitrite (109 g, 930.8 mmol, 3.00 eq.) at 55˜60° C. After all the isoamyl nitrite was added, the solution was stirred at 60° C. for 30 min. Then the mixture was concentrated under vacuum to give red solid. The solid was recrystallized with isopropyl alcohol to give 5-bromo-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile (110 g, 73%) as yellow solid.

Workup

  1. concentrationThen the mixture was concentrated under vacuum
  2. customto give red solid
  3. customThe solid was recrystallized with isopropyl alcohol

Sources & evidence

ORD record
ord-0986fed997c246acb91d89099e9f0ca3
Source dataset
uspto-grants-2016_03
Patent number
US09273007B2

Reaction notes

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